Need advice- young guy. older woman (women, attracted, younger, sex)

[cicare]

So basically, I've had this crush on a older woman who lives a few houses away from me for a number of years now. I finally managed to convince myself to go see her and tell her etc. I basically say "Hi, you're extremely attractive and I've wanted to say it for many years but couldn't bring myself to it" She responds by saying "Aww, thanks" and I left albeit a little awkward as she said it by not even opening her front door (Sort of see through mesh door where I could just make out her face).

I'm thinking of going back and asking straight up if she's interested in a sort of friends with benefits relationship or just friendship or just ask for her number but I'm not sure how that would turn out. What do you guys think? I'm 18 and I think she's around 35-40

[YAZ]

Way out of your league.

Judging by the way the encounter ended, you not figuring it out demonstrates this fact.

[usamathman]

Plenty of other attractive women out there. Don't waste anymore time in that one. Keep it moving.

[Shaquille]

You have to be more assertive, since she gave you that "aww", she probably already has you tagged as childish though lol. You should get more practice approaching younger women first, since you lack confidence. Cougars tend to gauge men on their confidence, lines won't be effective since they done heard them all before.

[MsAnnThrope]

LOL Awkward much?

Under no circumstances go back.

She would have opened the door if she was interested.

I can't believe you didn't pick up on this.

[BirdieBelle]

SO, if you're 18 and she's lived up the street from you for a "number of years," is it possible she has watched you "grow up"???

I want to tell all you "young" guys right now": STOP falling for all this movie bullsh*t about "friends with benefits."

In order to be friends with "benefits," you have to be FRIENDS first. You are not even that.

You can't just walk up to a woman and say, "I know I can barely talk to you, but I think you're hot and want you to have sex with me."

Yes, hook-ups and one-night stands do happen, but usually you have to put at least some effort into it.

To me, the age thing is not really a problem. It's the total lack of respect for her as a person that bugs me.

[srjth]

Hard to predict how it's going to turn out. Just go over there and tell her what you said but be prepared to have a conversation(s) with her (read: YOU have to guide the conversation) so she can warm up to you. Remember, she's not been thinking about you for years like you have been about her.

[atgss]

What I think will be the outcome?:

"And now, the end is here (you're not going to do her - lol!)
And so I face the final curtain (she's romantically out of your picture for good)
My friend, I'll say it clear (I hope you have it cleared up)
I'll state my case, of which I'm certain (by now you know there's no case and you should be certain of that)
I've lived a life that's full (and will continue to do after this)
I traveled each and ev'ry highway (and will do more of this)
And more, much more than this, I did it my way" (and will do other things your way)

[Ascension2012]

If you want a FWB type setup with this woman, become freinds first but dont forget to let her know in the process that you are sexualy attracted to her. Many women will not sleep with guys half their age, because they may be judged by others for it and it ensures your level of experience isnt equal hers.

[CSD610]

Originally Posted by cicare

So basically, I've had this crush on a older woman who lives a few houses away from me for a number of years now. I finally managed to convince myself to go see her and tell her etc. I basically say "Hi, you're extremely attractive and I've wanted to say it for many years but couldn't bring myself to it" She responds by saying "Aww, thanks" and I left albeit a little awkward as she said it by not even opening her front door (Sort of see through mesh door where I could just make out her face).

I'm thinking of going back and asking straight up if she's interested in a sort of friends with benefits relationship or just friendship or just ask for her number but I'm not sure how that would turn out. What do you guys think? I'm 18 and I think she's around 35-40

You seriously need to find a new hobby until you mature enough to figure out that a snowball has a better chance of surviving hades than you have experiencing sex with this woman.